Why I Chose to Work at a Startup

About 18 months ago, it was either Wichita, KS, Minneapolis, or stick in Chicago. The first two would have been great jobs that would have paid handsomely. The latter was a risk that I felt I could only take now, while I don’t have a wife and kids (and didn’t pay handsomely). I chose the latter, and couldn’t be happier with my decision.
I would argue that technology has never moved faster than it’s moving now. This opens up opportunities to work with new technologies and apply them to current systems,  processes, or business functions. The challenge of changing the way businesses function with new technology turns out to be such an abstract and difficult problem to solve. Striving to solve this problem and ultimately make the company successful is what drives people who work at a startup. The never ending search to solve this problem forces you to be a jack of all trades, which is why I love what I do. So here are my top reasons why I enjoy working at a startup and hopefully I can convert some of you.
1.) I’m emotionally invested
Aside from having equity and hoping to have a very lucrative payout via IPO or buyout, I find myself “drinking the kool-aid”. Some weeks when a prospect doesn’t sign a contract, you think you’ll be out of a job next week. Then when a big prospect signs a contract, you think it’ll be a matter of weeks before you’re on your yacht in the Mediterranean. Being emotionally invested in what we’re doing and how we’re trying to change the landscape of business gets me excited to go to work everyday and attempt to solve a problem that has never been solved before.
2.) I was sick of being a “number”
I’ve had jobs before where I just felt like if I left tomorrow, they’d just hire someone else to do the same thing. Regardless how much impact I tried to have, or how successful I was, I was caught  in the “corporate sludge”, impossible to get out. It was hard being motivated to go to work everyday. I felt like I could just punch in and punch out everyday, and that’s all I had to do; was just put in my time to work up the corporate ladder. And that’s what I want to stress, go somewhere where your voice is heard and you’re not just clocking in, expand your horizons, or go somewhere where you believe in the company’s mission. It will make waking up on Mondays much easier.
3.) Expanding my skill set
The things I’ve done to help “keep the doors open” are things I wouldn’t have done anywhere else. If you would’ve told me I’d have been project managing, product developing, involved in product strategy, doing client projects, coding, prospecting for clients, sales pitches, and doing User Experience testing all in a day’s work, I would’ve thought you were crazy. All of these are very transferable skill sets, especially in the new age workplace. By now, I can’t imagine going back to a company where all I did was one specific function.
End rant….
P.S. – If you feel like you can’t expand your horizons, make it a personal goal to learn something new every year. This past year for me it was computer programming. The knowledge is out there. You just need to be hungry enough to Google it…..


  1. Scott, this a great post. Glad you shared your experience, which I think can also apply to the world of starting up your own venture. I’m doing a little bit of both at the moment…working with a startup and starting up a business. It’s challenging, but exciting!

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